Trimethyl Phosphate → HCID 11524436, compound

HRID 2223773Notes

Reaction equation

HRID 2223773 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[C:10](=[O:27])[N:11]3[C:15]([CH2:18][C:19]4[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=4)([C:16]=2[OH:17])[CH2:14][CH2:13][CH2:12]3)[CH:5]=[C:6]([Cl:8])[CH:7]=1.P(OC)(OC)(O[CH3:31])=O.C([O-])([O-])=O.[K+].[K+]>O>[Cl:8][C:6]1[CH:5]=[C:4]([C:9]2[C:10](=[O:27])[N:11]3[C:15]([CH2:18][C:19]4[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=4)([C:16]=2[O:17][CH3:31])[CH2:14][CH2:13][CH2:12]3)[CH:3]=[C:2]([Cl:1])[CH:7]=1

Participants

5

Reactant 3

HCID 10541Trimethyl PhosphateHCID 11430Potassium CarbonateHCID 69194428HCID 69194428, compound

Product 1

HCID 11524436HCID 11524436, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-[6-(3,5-Dichloro-phenyl)-7-hydroxy-5-oxo-2,3-dihydro-1H,5H-pyrrolizin-7a-ylmethyl]-benzonitrile (24), (60 mg, 0.15 mmol) Trimethyl phosphate (4 ml) and K2CO3 were stirred under reflux for 10 hours then cooled to RT and diluted with water. The precipitate was filtered to afford after HPLC purification 4-[6-(3,5-Dichloro-phenyl)-7-methoxy-5-oxo-2,3-dihydro-1H,5H-pyrrolizin-7a-ylmethyl]-benzonitrile XII (18mg) as a white solid.

Workup

  1. temperatureunder reflux for 10 hours
  2. filtrationThe precipitate was filtered
  3. customto afford
  4. customafter HPLC purification 4-[6-(3,5-Dichloro-phenyl)-7-methoxy-5-oxo-2,3-dihydro-1H,5H-pyrrolizin-7a-ylmethyl]-benzonitrile XII (18mg) as a white solid

Sources & evidence

ORD record
ord-b123a9af328646aa8628512f171587f1
Source dataset
uspto-grants-2008_05
Patent number
US07375237B2

Reaction notes

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